Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes

Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C–H arylation. In the presence of a catalytic amount of Pd(OAc)(2), P(t-Bu(3))·HBF(4), and an excess of Cs(2)CO(3), the C–H arylation of TTF with several aryl br...

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Detalles Bibliográficos
Autores principales: Yoshimura, Aya, Kimura, Hitoshi, Kagawa, Kohei, Yoshioka, Mayuka, Itou, Toshiki, Vasu, Dhananjayan, Shirahata, Takashi, Yorimitsu, Hideki, Misaki, Yohji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237811/
https://www.ncbi.nlm.nih.gov/pubmed/32509028
http://dx.doi.org/10.3762/bjoc.16.86
Descripción
Sumario:Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C–H arylation. In the presence of a catalytic amount of Pd(OAc)(2), P(t-Bu(3))·HBF(4), and an excess of Cs(2)CO(3), the C–H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations.

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